Acridin-9-ylaminhydrochloridmonohydrat

less than 1 mg/mL at 72 °F (NTP, 1992)

1 G SOL IN 300 ML WATER & 150 ML ALCOHOL; SOL IN GLYCERIN

NEUTRAL REACTION; ONE OF THE MOST HIGHLY FLUORESCENT SUBSTANCES; 1 G DISSOLVED IN 300 ML WATER FORMS A FAINT YELLOW SOLN WITH BLUISH-VIOLET FLUORESCENCE

UV: 2125 (Sadtler Research Laboratories Spectral Collection) /9-Aminoacridine/

log Kow= 3.0 /9-aminoacridine/

Danger

H301 (66.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P318, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 9-Acridinamine, monohydrochloride

Aminacrine hydrochloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter).

STUDY WAS DESIGNED TO TEST POSSIBILITY THAT ETHIONINE MIGHT ACT AS INHIBITOR OF CERTAIN DNA METHYLATION REACTIONS, INCL METHYLATION OF ADENINE RESIDUES WHICH IS ASSOC WITH PRODUCT OF ESCHERICHIA COLI DAM+ GENE & PLAYS IMPORTANT PART IN MISMATCH REPAIR. IT WAS REASONED THAT INHIBITION OF GENE PRODUCT EQUIVALENT TO THE DAM+ GENE PRODUCT BY ETHIONINE IN SALMONELLA TYPHIMURIUM MIGHT MAKE THE CELLS PHENOTYPICALLY DAM-, IN WHICH CASE THEY SHOULD RESEMBLE THE ESCHERICHIA COLI DAM MUTANTS IN BEING HYPERMUTABLE BY 2-AMINOPURINE & 9-AMINOACRIDINE. RESULTS SHOW THAT ETHIONINE DOES SLIGHTLY ENHANCE YIELD OF TRP+ REVERTANTS OBTAINED FROM BASE-PAIR SUBSTITUTION SALMONELLA TYPHIMURIUM STRAIN TRPE8 FOLLOWING TREATMENT WITH 2-AMINOPURINE, BUT THAT IT EXERTS VERY POWERFUL ANTIMUTAGENIC EFFECT IN CELLS OF STRAIN TA1537 TREATED WITH FRAMESHIFT MUTAGEN 9-AMINOACRIDINE.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=134-50-9]

...MODERATELY INJURIOUS TO RABBIT EYES.

IN FIBROBLAST CELL LINES FROM RAINBOW TROUT GONAD, BLUEGILL FRY & STEELHEAD EMBRYO INCUBATED IN PRESENCE OF 8 MUTAGENS (INCL 9-AMINOACRIDINE) AT VARIOUS CONCN FOR 72 HR, THE NUMBER OF CELLS CONTINUED TO DECLINE IN DIRECT PROPORTION TO AMT OF CHEM IN MEDIA. THIS REPRESENTED INCR TOXICITY AS CONCN OF MUTAGEN INCR. THIS RESPONSE WAS THE RESULT OF TREATED CELLS NOT DIVIDING, WHILE UNTREATED CONTROLS CONTINUED TO REPLICATE. BLUEGILL FRY CELLS WERE MOST SUSCEPTIBLE TO TOXIC EFFECT.

TESTICULAR CELLS OF MALE MICE WERE ISOLATED, & INCORPORATION OF TRITIUM LABELED THYMIDINE INTO DNA OF CELLS WAS ESTIMATED AFTER EXPOSURE TO VARIOUS CHEMICAL MUTAGENS. NORMAL SEMICONSERVATIVE DNA SYNTH WAS SUPPRESSED BY ADDN OF HYDROXYUREA WHICH WAS USED AS CONTROL. 8/13 TEST CHEM STIMULATED UNSCHEDULED DNA SYNTHESIS. 9-AMINOACRIDINE & THE REMAINING 4 TEST CHEM DID NOT INDUCE UNSCHEDULED DNA SYNTHESIS, EVEN WHEN INCUBATION PERIODS WITH CELLS WERE PROLONGED, & CONCN OF COMPD INCR TO BEGINNING OF TOXIC EFFECTS.

9-Aminoacridine hydrochloride (9AH) ... was tested for its effects on reproduction & fertility in CD-1 mice using the NTP Report # RACB protocol. Data from a two wk dose-range-finding study (Task 1) were used to set exposure concns for the Task 2 continuous cohabitation study at 0.025, 0.05, & 0.1% in feed. Based on body weights & food consumption data, the estimated daily doses were nearly equal to 31, 66, & 145 mg/kg. One male & 2 female control mice, & one female in the middle dose group, died during the 18 wk Task 2 cohabitation phase. While the male mice in the high dose group gained less weight than controls, only high dose female mean body weights were significantly lower than control means during the study, by nearly equal to 10%. While 9AH consumption did not alter the number of litters/pair, the number of pups/litter or their viability, the pup weight adjusted for body weight was reduced by 9% in the high dose group. This pup weight reduction may be related to the reduced postpartum dam weights. In the absence of changes in F0 fertility parameters, Task 3 was not conducted, & the last litter from the control, middle, & high dose groups was reared by their dams. Approx 2/3rds of the pups in the high dose group died before /postnatal day/ 14, & pup weight at all times until weaning was reduced by nearly equal to 30%. Pup survival & weight gain in the middle dose group were not changed. The increased morbidity at the high dose left insufficient pups to evaluate for fertility effects. Thus, Task 4 was performed using controls & middle dose group mice. During the Task 4 mating trial, 9AH had no effect on the number of pups/litter, or their viability or weight. Thus, there was no adverse reproductive effect noted in the second generation at 0.05% 9AH. After the F2 pups were delivered & evaluated, the F1 adults were killed & necropsied. While female body weights at the middle dose were not changed, liver weight was increased by nearly equal to 30%, & adjusted kidney weights were reduced by nearly equal to 10%. For treated males, body weight was reduced by nearly equal to 10%, while adjusted liver weight was increased by nearly equal to 25%. Sperm indices at necropsy were unchanged, as was estrous cycle length. Thus, 9AH induced some developmental toxicity, in the form of reduced F1 pup weight, at the same dose that also reduced dam weight, & at doses > those that increased F1 liver weight. No changes in other fertility indices were observed. These data suggest that , for 9AH, the hepatic effects are > any reproductive effects. Developmental toxicity could not be separated from the general toxicity.

IN PRESENCE OF 9-AMINOACRIDINE-HCL, BACTERIOPHAGE P22 OF SALMONELLA TYPHIMURIUM WAS KILLED ON IRRADIATION WITH VISIBLE LIGHT; NEITHER THE COMPD NOR THE LIGHT ALONE INACTIVATED THE PHAGE. THE ACRIDINE INDUCED DAMAGE IN THE PHAGES BY 4 INDEPENDENT MODES: 1) FROM SHIFT MUTAGENESIS DURING PHAGE DNA REPLICATION; 2) ACRIDINE-SENSITIZED PHYTOTOXICITY TO PHAGE PARTICLES; 3) ACRIDINE-SENSITIZED PHOTOMUTAGENESIS; AND 4) INTERFERENCE WITH VIRUS ASSEMBLY. KINETIC ANALYSIS OF FORMATION & PHOTOINACTIVATION OF COMPLEX BETWEEN 9-AMINOACRIDINE-HCL & P22 INDICATED THAT ACRIDINES BOUND TO DNA BACKBONE & INTERCALATED BETWEEN THE BASIS COULD MEDIATE LETHAL DAMAGE TO DNA-INJECTION PROTEINS.

INFLUENCE OF SELF-COMPLEMENTARY OLIGODEOXYNUCLEOTIDES ON CHEMICAL SHIFTS OF PROTONS OF MUTAGENIC 9-AMINOACRIDINE WAS MEASURED. UPFIELD SHIFTS INDICATIVE OF INTERCALATIVE BINDING ARE FOUND IN CASES OF DG-DC, DC-DG & DA-DT-DG-DC-DA-DT BUT NOT IN DA-DT. GEOMETRIES FOR COMPLEXES ARE COMPATIBLE WITH CHEMICAL-SHIFT DATA & X-RAY STRUCTURE OF COMPLEX BETWEEN RI5C-RG & 9-AMINOACRIDINE DETERMINED BY SAKORE ET AL CAN BE IDENTIFIED USING RECENT THEORETICAL ESTIMATES OF SHIFTS INDUCED BY NUCLEOTIDE BASES.

INTERACTIONS OF 9-AMINOACRIDINE-HCL WITH IONIC CHANNELS WERE STUDIED IN INTERNALLY PERFUSED SQUID AXONS. KINETICS OF BLOCK OF SODIUM CHANNELS WITH 9-AMINOACRIDINE-HCL VARIED DEPENDING ON VOLTAGE-CLAMP PULSES & THE STATE OF GATING MACHINERY OFF SODIUM CHANNELS. IN AN AXON WITH INTACT H GATE, THE BLOCK EXHIBITED FREQUENCY- & VOLTAGE-DEPENDENT CHARACTERISTICS. IT ALSO BLOCKED POTASSIUM CHANNELS.

EFFECT OF SEQUENCE ON BINDING TO DNA WAS INVESTIGATED BY STUDYING ITS INTERACTION WITH DEOXYDINUCLEOSIDE PHOSPHATES OF DIFFERENT SEQUENCES USING PNMR. SIMPLEST MODEL THAT FITS THE DATA INCL 1) DIMERIZATION OF 9-AMINOACRIDINE AND 2) A MIXTURE OF 1:1 & 2:1 (DINUCLEOSIDE PHOSPHATE/9-AMINOACRIDINE) COMPLEXES. THE 1:1 COMPLEXES SEEM TO INVOLVE INTERACTION OF THE RING NITROGEN WITH THE BACKBONE PHOSPHATE & STACKING OF ONE OR BOTH CHROMOPHORES ON THE ACRIDINE; PREFERENCE IN BINDING WAS OBSERVED FOR ALTERNATING (PURINE-PYRIMIDINE OR PYRIMIDINE-PURINE) OVER NON-ALTERNATING (PURINE-PURINE) DINUCLEOSIDE PHOSPHATES. THE 2:1 COMPLEXES INVOLVE INTERCALATION OF ACRIDINE BETWEEN 2 COMPLEMENTARY DINUCLEOSIDE PHOSPHATE STRANDS WITH WEAK SEQUENCE PREFERENCES IN BINDING. STEREOCHEMISTRY OF INTERACTION DIFFERS BETWEEN NON-ALTERNATING PURINE-PURINE SEQUENCES & ALTERNATING PYRIMIDINE-PURINE OR PURINE-PYRIMIDINE SEQUENCES IN HAVING 9-AMINOACRIDINE STACKED WITH PURINES OF 1 STRAND RATHER THAN STRADDLING PURINES ON OPPOSITE STRANDS. DIFFERENCES IN STEREOCHEMISTRY COULD POSSIBLY BE DETERMINING FACTOR IN FRAMESHIFT SEQUENCE SPECIFICITY.

For more Mechanism of Action (Complete) data for 9-AMINOACRIDINE HYDROCHLORIDE (6 total), please visit the HSDB record page.

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

USED EXPERIMENTALLY AS A PROBE FOR BIOLOGICAL MEMBRANES AND DNA

MEDICATION (VET)

MEDICATION

9-Acridinamine, hydrochloride (1:1): INACTIVE

USED AS REFERENCE COMPD IN THE VISCOMETRIC ANALYSIS OF CLOSED CIRCULAR DNA COMBINED WITH SPECTROPHOTOMETRIC & FLUOROMETRIC STUDIES TO CHARACTERIZE THE MODE OF DNA BINDING OF ANTITRYPANOSOMAL & ANTITUMOR COMPOUNDS.